4-Hydroxybenzaldehyde → 1-[2-(4-Cyanophenyl)ethyl]-4-(4-formylphenoxymethyl)piperidin-4-ol

HRID 967765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967765
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]3([CH2:16][O:15]3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[OH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:18][CH2:17][C:14]([CH2:16][O:19][C:20]3[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=3)([OH:15])[CH2:13][CH2:12]2)=[CH:7][CH:8]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 858197211-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxirane

Produkt 1

HCID 222912951-[2-(4-Cyanophenyl)ethyl]-4-(4-formylphenoxymethyl)piperidin-4-olAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The compound (10.0 g) obtained in Step 3 of Example 1 and 4-hydroxybenzaldehyde (5.04 g) were dissolved in anhydrous dimethylformamide (55 mL), and to the mixture was added potassium carbonate (28.5 g) and 18-crown-6 (1.09 g) at room temperature under nitrogen atmosphere and the mixture was heated at 100° C. for five hours. After allowing to cool, insoluble matter was removed by filtration and washed with ethyl acetate (300 mL). The filtrate was cooled with ice-water and water (150 mL) was added to the mixture to be separated. The aqueous layer was extracted with ethyl acetate. The organic layer was combined, washed with water and brine successively, and dried over anhydrous sodium sulfate, followed by removal of the solvent under reduced pressure. The obtained residue was crystallized from ether and collected by filtration to obtain the titled compound (12.7 g) as crystals.

Aufarbeitung

  1. temperatureto cool
  2. custominsoluble matter was removed by filtration
  3. washwashed with ethyl acetate (300 mL)
  4. temperatureThe filtrate was cooled with ice-water and water (150 mL)
  5. additionwas added to the mixture
  6. customto be separated
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washwashed with water and brine successively
  9. dry with materialdried over anhydrous sodium sulfate
  10. customfollowed by removal of the solvent under reduced pressure
  11. customThe obtained residue was crystallized from ether
  12. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e38dba8b0eeb4cd89a41c6e55a3df14a
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956046B2

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